


First Time Confusion

by thegreatficmaster



Series: Supernatural Collection [32]
Category: Supernatural
Genre: Biting, M/M, Reader-Insert, Smut
Language: English
Status: Completed
Published: 2019-07-17
Updated: 2019-07-17
Packaged: 2020-06-30 03:06:34
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,350
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19844281
Author URL: https://archiveofourown.org/users/thegreatficmaster/pseuds/thegreatficmaster
Summary: Who knew Sam would turn you?





	First Time Confusion

“Seriously, y/n. You’re staring again”, Dean stated in a hushed whisper, y/n snapping his gaze away from the tall Winchester and to the older one, his eyes wide.

“Wh-what? Staring? Staring at what?” he asked, trying to avoid his obvious attraction to Sam.

Dean rolled his eyes in frustration. 

He was sick of both men skating around their feelings for each other. 

He understood why y/n tried to avoid them. 

Y/n was completely straight. 

Or, as straight as you could be. 

He never had any sort of sexual experience, or attraction to another guy before. 

But Sam was different. 

His long beautiful hair. His sparkling eyes. The sexy body. 

Y/n was so confused by the feelings and emotions Sam brought out in him.

But Dean had no idea why Sam wasn’t making a move. 

Sam had a few experiences with men in the past. 

Dean had caught Sam with one during a case once.

The older Winchester was shocked to say the least, but he accepted it. 

He had no problem with Sam’s sexual orientation. 

Just as long as he kept it within his own room and out of Baby.

But Sam had said nothing to y/n. 

Dean knew he was obviously attracted to the new member of their family. 

Sam would stare, just as much as y/n would. 

He’d ask Dean if he knew whether y/n was dating anyone. Or if he went home with someone when Dean would arrive earlier from the closest bar. 

So Dean decided he would have to do something himself.

The next day, Dean called y/n into his room, texting Sam, so he knew when his brother came back, instructing him to come straight to his room. 

As soon as he confirmed Sam was going to be back soon, he began talking to y/n, trying to get him to admit his feelings, so his plan would be successful. 

“So, y/n. Why the hell aren’t you doing anything?”

“What do you mean, doing anything? There’s nothing to be done”, he replied, trying to avoid the topic so he wouldn’t have to deal with these new feelings.

Dean sighed in exasperation.

“Seriously, dude! You stare all day long, you smile when he says stupid shit and you literally talk about him all the time, until you realise it”, Dean listed, wanting y/n to finally accept it.

“I don’t know, Dean. I mean-I’m straight. Well, I think I am”, he said, opening up to the older Winchester, the man being his best friend.

“But with Sam, I don’t know. I just feel something. But it’s just weird. I’ve never had feelings for a guy. Do you know how confusing that is?”

Dean nodded, not really able to understand specifically, but sympathising. 

“I-I get it. I do. But, maybe you should talk to him about it. See if he can help with it”, Dean suggested.

Y/n scoffed. 

“Are you serious? You really think I have any sort of a chance with Sam?” he questioned, doubting the other Winchester would ever be interested.

“I mean, why don’t you just ask me?” a voice interrupted, y/n whipping his head around to the door, to see the younger Winchester stood there, a smile on his dumb perfect face.

Y/n glared back at Dean, knowing he did this on purpose.

“I’m-uh-just gonna leave you two alone”, he said, getting off the bed and patting Sam on the shoulder, winking at y/n, before making his way to the kitchen, wanting some more pie.

“So, you don’t think you have a chance with me?” Sam asked, trying to lighten the tense mood in the room.

“I-I mean-I-I don’t know”, y/n sighed out, really just wanting to sink into the bed and never come back out.

“Because, you do, you know”. 

Y/n looked up at the man, shocked at what he heard.

“Wh-what?”

“I said, you do have a chance. I’ve liked you since we met, y/n. And spending time with you just makes me want to know you even more. So, maybe, I don’t know, you wanna go on a date?” he asked, running his hands through his hair nervously, staring at y/n anticipating his answer.

Y/n smiled, nodding shyly.

“I-I’d like that”, he replied quietly, to which Sam grinned, the men leaving Dean’s bedroom and making their way to the kitchen.

It had been almost a month since y/n and Sam had started dating. 

They went on dates whenever they could. Whether it was in a bar, a diner, or just staying in the library or Sam’s room, watching a movie or reading some books.

They always found ways to spend time together.

“Hey, Sam”, y/n called out to his boyfriend, while they were sat in the library.

“Yea?”

“I was thinking, maybe we could try it today”, he said.

Sam looked up from his book, eyebrows lifting in confusion.

“Try what?”

“You know”, he said, nodding his head in an attempt to get the man to understand.

“No. I don’t know”.

“Sex”, y/n rushed out.

Sam laughed to himself.

“You do realize Dean isn’t in, don’t you?”

Y/n’s eyes widened, embarrassed.

“Oh”.

Sam stood up, making his way over to y/n and looked into his eyes, leaning with his hands on the arms of the chair, his face close to y/n’s.

“Are you sure you want to? I don’t mind waiting”.

“I’m sure. I just- I need something. I haven’t even wanked since we started dating”, y/n explained. 

Sam’s eyes widened at this, his tongue darting out to lick his lips. 

He loved when men would go a while without cumming. That way, when they finally came, their load was huge and he could see the creamy fluid shoot out of their beautiful cocks.

Leaning forward, Sam took y/n into possessive kiss, his dick already twitching at the thought of finally having sex with y/n.

Dragging him off the chair, Sam pulled y/n out of the library and to his room, determined to do this.

As soon as they entered, Sam shut the door and threw y/n onto the bed, jumping on top of him and kissing him, tongues sliding over lips, teeth clashing, a wet shine all around y/n’s lips from the sloppiness of the kiss.

Y/n moaned at the feeling of Sam’s wet tongue, gliding over his own then down his neck, teeth nibbling on his skin.

“Shit, Sam”, he whined, a hand clutching some hair, loving the feeling of the soft silky strands in between his fingers. 

Sam kept moving down, taking off y/n’s shirt and his own, his hands rubbing down y/n’s firm chest, as y/n wrapped his other arm around Sam’s firm back, feeling the way the muscles rolled.

Sam kept up his actions, y/n’s dick hard as a rock and wet from the precum leaking out. 

Sam lifted his head when he realized they hadn’t discussed anything.

“Wait, how do you wanna do this?” he asked.

Y/n gave him a confused look.

“What do you mean?”

“I mean, are you gonna be the bottom? Or am I?” the Winchester asked.

“What the hell is a bottom?”

Y/n had zero information about gay sex. 

He was never really interested in guys at all, so he had no idea about the ways they did things.

Sam sat up, pulling y/n with him.

“Ok, so, basically, a top is the person who fuck. A bottom is the person who gets fucked”, he explained.

“Ok. And what are you then?”

“I’m a top”, he said, puffing his chest up to make sure y/n knew that he was the one to be doing the fucking.

“So, th-that means I’m-I’m a bottom then?” y/n asked, slightly frightened as to what this would entail.

Sam smirked, knowing he would have that ass soon.

“Yep. But don’t worry, I’m gonna take real good care of you”. 

Y/n nodded, trusting Sam completely, but at the same time frightened as hell.

“Ok, I’m gonna open you up first, ok?”

Y/n couldn’t say anything, his head nodding the slightest amount.

Sam took y/n’s pants off along with his own, showing off his huge thick cock, while y/n showed off his considerable dick as well.

Sam leaned down kissing y/n as he circled y/n’s ass with his fingers, the muscles twitching.

“I’m going in now”.

Sam inserted his index finger, barely two centimetres when the muscles contracted completely, y/n tensing at the completely foreign feeling, trapping Sam’s finger in his hole.

“Whoa whoa whoa”, he rushed out, running his hands down y/n’s arm.

“You need to relax for this, y/n/n. Just, calm down. Close your eyes and take a few deep breaths. Ok?”

Y/n nodded, the feeling of Sam’s hand on his chest, tracing lines, relaxed him, his hole granting access to Sam’s finger, which slipped in almost completely, y/n’s eyes shooting open at the amazing feeling.

“Damn, that’s so good”, he whispered, breathing too heavily to be heard properly.

“If you think that’s good, wait till I get my dick inside you. You want that?” he whispered into y/n’s ears, nibbling on them slightly. 

“You’ll feel me all the way inside your stomach.” 

Sam pressed a hand to y/n’s stomach, pressing down firmly as his finger stroked along his inner walls. 

“You’ll feel me tomorrow. And the day after. And after that too. And you wanna know the best part? You’ll be begging for more by the time I’m done with you.”

Y/n nodded, breathlessly by this point.

“Yes, Sam. Please. More”.

Sam chuckled, getting to work on opening up y/n’s tight ass, adding more fingers each time, y/n squealing at the newfound pleasure. 

If only he knew he had a thing for men all this time. 

He would have been doing this from the start. 

Then again, it was only Sam he had a thing for.

“I’ve opened you up good now, baby”, Sam said, sticking his fingers into his mouth and slurping on them, the sight sending blood rushing to y/n’s already straining cock.

Sam picked y/n up and bent him over the chair, one of his legs on the ground while Sam held the other up at an angle, y/n’s hole on display perfectly.

“You know how long I’ve wanted this? Hmm?” Sam asked, licking at the spot behind y/n’s ear, his cock pushing at the hole, but not entering yet.

“Wanted you since day one. You looked so amazing. I could see your boner in those jeans you know. When you were looking at me. After the blood of that demon poured onto my shirt. I could see you. Wanted to fuck you right there and then. But Dean was there. He’s not now though”.

Sam thrust in right after that, completely stretching y/n’s hole, burning slightly.

“Shit, Sam” he gasped, taking in a deep breath. 

“It hurts”.

“I know it does, but just relax. It’ll hurt a little more, but it’s gonna feel real good soon. You trust me, right?”

“Yea.Yea, I trust you”.

“Then just bear with me”.

Sam slid out slowly, his tip almost completely out, before thrusting back in, gently, making sure y/n would get used to this.

He could hear y/n’s breath, still laboured from discomfort and continued this slow pace, until he began sliding in and out at a faster rate, hearing how y/n was now moaning in pleasure.

Y/n had his eyes shut, gripping onto the arm of the chair. 

The feeling of Sam’s thick cock inside him was so amazing. 

He wondered if this was how the women he fucked felt.

The feeling of a big thick dick inside them, filling them up, over and over, stretching their tight little holes.

Sam was just as amazed. 

He’d slept with guys before, knowing their asses were always tighter than a pussy. 

But y/n’s was the tightest, warmest hole he’d ever had. 

The way it engulfed his dick was beautiful.

He just stared at the way it disappeared into the hole, like it belonged in there.

Sam lay his head on y/n’s back, biting down hard, y/n screaming in both pain and pleasure. 

But he was too deep in the euphoric state right now to be able to say anything.

Sam kept pounding into y/n, hitting prostate over and over, the familiar build up making y/n just want to explode.

“Yea, baby. I feel you tightening, y'know? Gonna cum? Hmm? Well, you’re not doing it on the chair”.

Sam pulled out, leaving y/n feeling empty, but not for long as Sam threw y/n onto the bed and immediately thrust back in, pounding into y/n as he bit down on his shoulder, biting and marking y/n, sucking hickeys onto his skin, making sure the world would know who he belonged to.

“Sam, I think I’m gon-gonna-oh fuuuuckkk!!!” he gritted out, his orgasm hitting him, rope after rope of cum splashing onto his chest and abs, the biggest cumshot Sam had ever seen, who came immediately from the sight, clenching his jaw as he shot his load into y/n.

The men stayed like that for a while, Sam leaning forward and collecting some of the cum in his mouth, pulling out, before situating his face in front of y/n’s red puffy asshole, inserting y/n’s own cum into his ass using his tongue, mixing it with his own, loving the taste of y/n’s ass filled with both of their cum.

They settled into the bed, panting and catching their breaths, sweaty and spent. 

Y/n lay his head on Sam’s hairy chest, nuzzling his nose into the wet hairs, placing a kiss over Sam’s heart. 

Sam kissed y/n’s temple, both men falling into a blissful sleep. 


End file.
